| 1. Round | 31/07/2018 | Krylia Sovetov | - | CSKA Moskva | 0:0 | ||||
| 2. Round | 05/08/2018 | Krylia Sovetov | - | FK Orenburg | 0:3 | ||||
| 3. Round | 11/08/2018 | FK Rostov | - | Krylia Sovetov | 0:1 | ||||
| 4. Round | 19/08/2018 | Krylia Sovetov | - | Lokomotiv Moskva | 0:1 |  |
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| 5. Round | 27/08/2018 | Enisey Krasnoyarsk | - | Krylia Sovetov | 1:0 | ||||
| 6. Round | 01/09/2018 | Krylia Sovetov | - | Anzhi Makhachkala | 1:0 | ||||
| 12. Round | 29/10/2018 | Krylia Sovetov | - | Zenit St. Petersburg | 0:1 | ||||
| 13. Round | 05/11/2018 | FK Ufa | - | Krylia Sovetov | 1:2 |  |
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| 14. Round | 10/11/2018 | Krylia Sovetov | - | Akhmat Grozny | 1:2 | ||||
| 15. Round | 25/11/2018 | Spartak Moskva | - | Krylia Sovetov | 3:1 | ||||
| 17. Round | 08/12/2018 | Krylia Sovetov | - | FK Rostov | 1:0 | ||||
| 21. Round | 29/03/2019 | Krylia Sovetov | - | Arsenal Tula | 0:1 | ||||
| 26. Round | 28/04/2019 | Zenit St. Petersburg | - | Krylia Sovetov | 4:2 | ||||
| 27. Round | 05/05/2019 | Krylia Sovetov | - | FK Ufa | 1:1 | ||||
| 28. Round | 11/05/2019 | Akhmat Grozny | - | Krylia Sovetov | 2:1 | ||||
| 29. Round | 18/05/2019 | Krylia Sovetov | - | Spartak Moskva | 1:2 | ||||
| 30. Round | 26/05/2019 | CSKA Moskva | - | Krylia Sovetov | 6:0 |
Russia